Getting There. A stretch limo sent by Bom­bardier Flexjet—a fractional and flight-card provider with a fleet of Bombardier business jets—carries the travelers from their homes to the Signature Flight Support general-aviation facility at Teterboro Airport in New Jersey. One of the couples has purchased a 25-hour Flexjet 25 card, which “gives you access to Flexjet’s entire flight-card fleet,” says company vice president Sylvain Levesque. “These couples could spread out in comfort in the Challenger 604, the largest and most advanced member of this fleet.” ?The trip to Napa County Airport takes about five hours in the 604, and the $147,000 round-trip fee is applied to the $309,900 cost of the card. ?A limo sent by BeautifulPlaces transports the couples to St. Helena, about 45 minutes away.

Villa. “When couples travel together, they want a place that’s going to inspire them to spend time together and renew friendships,” says Liza Graves, the owner and head of marketing for the Sonoma, Calif.–based vacation-rentals company BeautifulPlaces. For this group, Graves says, that spot is Vista del Lago, a new, ?Tuscan-style, four-bedroom villa set on 120 acres overlooking Lake Hennessey. “There are plenty of hang-out spaces,” says Graves, noting the home’s indoor and outdoor kitchens and living and dining rooms. BeautifulPlaces hires staff for ?Vista del Lago, which rents for a base rate of $20,300 per week, based on each client’s specifications. “For this group,” says Graves, “I’d recommend somebody to provide housekeeping and light cooking, and to run errands.”

Experience. Graves also suggests that the couples bring in various chefs for a true sampling of Napa Valley’s culinary delights. “We would arrange very special menus,” she says. “They might say, ‘We want an incredible Syrah-pairing menu,’ or ‘We want something incredibly eclectic.’ We can arrange for someone like chef Douglas Keane from the Michelin-two-star restaurant Cyrus in Healdsburg to come to the villa.” ?The couples also would have the opportunity to sample vintages with some of Napa Valley’s leading winemakers. “Imagine sitting by that pool and having a private tasting,” Graves says, adding that Andy Erickson, winemaker at the legendary, closed-to-the-public winery Screaming Eagle, could serve as host. Wine-related activities off-site might include “working the harvest, either picking grapes or participating in blending,” she says, “and we can arrange for a winemaker to produce a custom blend.” Should the New Yorkers find wine-country living a bit slow, they can pick up the pace at Sonoma’s Infineon Raceway, where Graves and her staff will arrange private driving lessons and the opportunity to race the 2.52-mile, 12-turn course.